Methyl acetoacetate → HCID 54682304, compound

HRID 356523Notes

Reaction equation

HRID 356523 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[CH3:16][CH:17]([CH3:30])[CH2:18][CH2:19][C:20](=[O:29])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CCCCCC.O.C1COCC1>[OH:4][C:3]1[CH2:5][C:20]([CH2:19][CH2:18][CH:17]([CH3:30])[CH3:16])([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:29][C:1](=[O:6])[CH:2]=1

Participants

8

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 4301992HCID 4301992, compoundHCID 178418339Butyllithium

Product 1

HCID 54682304HCID 54682304, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared as described in General Method 5 using 2.56 g (22 mmol) of methyl acetoacetate, 0.97 g (24.2 mmol) of NaH 60% dispersion in oil, 14.4 mL (23.1 mmol) of 1.6M n-butyl lithium in hexane, 4.5 g (22.0 mmol) of 6-methyl-1-phenyl-heptan-3-one (A. Katritzky, et al., J. Org. Chem., 1995, 60 (23), 7605) and 60 mL of THF. After addition of the ketone, the reaction was stirred for 90 minutes at 0° C. and then for 30 minutes at room temperature. Water (400 mL) was slowly added with vigorous stirring, and the reaction was allowed to stir overnight. The reaction was worked up as in General Method 6. The product was triturated from ether to afford a solid, m.p. 99°-100.5° C. 1H NMR (CDCl3) δ 0.89-0.92 (d,d, 6 H), 1.24-1.32 (m, 2 H), 1.48-1.57 (m, 1 H), 1.64-1.83 (m, 2 H), 1.94-2.03 (m, 2 H), 2.68-2.77 (m, s, 4 H), 3.42 (s, 2 H), 7.16-7.32 (m, 5 H).

Workup

  1. waitfor 30 minutes at room temperature
  2. stirringto stir overnight
  3. customThe product was triturated from ether
  4. customto afford a solid, m.p. 99°-100.5° C

Sources & evidence

ORD record
ord-8c0ef912773343d48a0d87de53e7f6ef
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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